As is generally known in prior art, chelating phosphine compounds when bound to metal atoms are useful as catalysts. To facilitate separation of the catalysts from a chemical process, phosphorus ligands have been attached to solid supports such as polymers (“Supported Metal Complexes”, D. Reidel Publishing, 1985; Acta. Polymer. 1996, 47, 1; “Chem. Met.-Carbon Bond”, Hartley, F. R (Ed), 1987, vol. 4, pp. 1163-1225; Neckers, J. Macromol. Sci., Chem. 1987, A24, 431-48). Interest in using the combinatorial “split and mix synthesis” approach to generate polymer-bound ligands which could be tested as catalysts has brought to fore the importance of new chemistry with which to attach phosphine ligands to polymer supports (Balkenhohl et al., Angew. Chem., Int. Ed. Engl. 1996, 35, 2288-2337; Gilbertson et al., J. Organometallics 1996, 15, 4678-4680; Gilbertson et al., J. Am. Chem. Soc. 1994, 116, 4481-4482).
Novel processes have been discovered to prepare new compositions of matter that contain chelating phosphine compounds, including compounds of asymmetric diphosphines. Phosphine compounds have been shown to be useful when combined with transition metals as catalysts for chemical processes. The processes can also be utilized in a combinatorial scheme to produce libraries of phosphine compounds.
Addition of aldehyde in salicylaldehydes to acetylenes is known, but is unknown for addition to alkenes. (Kokai Tokkyo Koho JP 7853632; JP 76128205 Kokubo et al., J. Org. Chem. 1997, 62, 4564-4565.) The new phosphorus compounds have been shown to be useful as ligands in catalysts for the decarbonylation of the salicylaldehyde and insertion of the alkene, followed by ring closure forming a coumarin.